| EIU Showdown | 08/28/2019 | Woodridge, IL | Downers Grove North HS - Green Valley Forest Preserve |
| Plainfield City Championships | 08/31/2019 | Plainfield , IL | Plainfield Park District - Van Horn Woods |
| Plainfield North Tiger Relays | 09/04/2019 | , | - |
| Peoria First to the Finish Invitational | 09/14/2019 | Peoria, IL | - Detweiller Park |
| Minooka Flight Invite | 09/21/2019 | Channahon, IL | Minooka High School - Channahon Community Park |
| York F/S Invite | 09/23/2019 | , | - |
| Palatine Meet of Champions | 09/28/2019 | Palatine, IL | Palatine High School - Deer Grove East Forest Preserve |
| Triangle Meet - Plainfield North, Oswego East, Minooka | 10/02/2019 | , | - |
| Locktoberfest Invitational | 10/05/2019 | , | - |
| New Balance/Naperville Running Co. Twilight Invite | 10/09/2019 | Naperville, IL | Naperville North High School - Cross Country Course |
| SPC Conference Championship | 10/18/2019 | Channahon, IL | Minooka High School - Channahon Community Park |
| Buffalo Grove F/S Race Car Invite | 10/22/2019 | Buffalo Grove, IL | Buffalo Grove High School - Willow Stream Park |
| IHSA Regional | 10/26/2019 | Shorewood, IL | Plainfield South (IL) High School - Hammel Woods |
| IHSA Sectional - Lyon's Township High School | 11/02/2019 | Western Springs, IL | Lyons Township High School - South Campus Cross Country Course |
| Plainfield Central Time Trial | 11/07/2019 | Plainfield, IL | Plainfield Central - South grounds |
| IHSA 3A State Cross Country Championships | 11/08/2019 - 11/09/2019 | Peoria, IL | - Detweiller Park |
| NXN Midwest Regional | 11/17/2019 | Terre Haute, IN | Indiana State University - LaVern Gibson Championship Cross Country Course |
| FootLocker Midwest Regional | 11/30/2019 | Kenosha, WI | University of Wisconsin–Parkside - Wayne E. Dannehl National Cross Country Course |
